Crystal structure, Hirshfeld surface analysis and inter­action energy, DFT and anti­bacterial activity studies of ethyl 2-[(2Z)-2-(2-chloro­benzyl­idene)-3-oxo-3,4-di­hydro-2H-1,4-benzo­thia­zin-4-yl]acetate

. 2020 Apr 7;76(Pt 5):629–636. doi: 10.1107/S2056989020004119

Cl1—C11	1.741 (2)	C9—C10	1.465 (3)
S1—C6	1.755 (2)	C9—H9	0.95 (2)
S1—C7	1.757 (2)	C10—C15	1.401 (3)
O1—C8	1.224 (2)	C10—C11	1.405 (3)
O2—C17	1.200 (2)	C11—C12	1.382 (3)
O3—C17	1.335 (2)	C12—C13	1.383 (3)
O3—C18	1.462 (3)	C12—H12	0.95 (3)
N1—C8	1.381 (2)	C13—C14	1.390 (3)
N1—C1	1.417 (2)	C13—H13	0.96 (3)
N1—C16	1.452 (2)	C14—C15	1.382 (3)
C1—C2	1.395 (3)	C14—H14	0.97 (3)
C1—C6	1.397 (3)	C15—H15	0.95 (2)
C2—C3	1.386 (3)	C16—C17	1.515 (3)
C2—H2	0.95 (3)	C16—H16A	0.96 (3)
C3—C4	1.382 (3)	C16—H16B	0.92 (3)
C3—H3	0.94 (3)	C18—C19	1.498 (4)
C4—C5	1.384 (3)	C18—H18A	0.99 (3)
C4—H4	0.93 (3)	C18—H18B	1.00 (3)
C5—C6	1.392 (3)	C19—H19A	1.03 (3)
C5—H5	0.96 (3)	C19—H19B	0.94 (4)
C7—C9	1.343 (3)	C19—H19C	1.00 (4)
C7—C8	1.490 (3)

Cl1···C14ⁱ	3.5363 (9)	O1···H12ⁱ	2.560 (9)
Cl1···S1ⁱ	3.7268 (3)	O1···H15ⁱⁱ	2.400 (8)
Cl1···C10ⁱ	3.5940 (7)	O2···H18B	2.545 (11)
Cl1···C15ⁱ	3.4359 (7)	O2···H13ⁱ	2.606 (10)
Cl1···H9	2.674 (8)	O2···H18A	2.74 (3)
S1···N1	3.0100 (6)	O3···H16B^vi	2.666 (8)
S1···C15	3.1748 (8)	C2···C17	3.2932 (10)
S1···O1ⁱⁱ	3.4189 (6)	C4···C14ⁱⁱⁱ	3.5882 (12)
S1···H15	2.660 (10)	C2···H16B	2.621 (8)
S1···H5ⁱⁱⁱ	2.906 (9)	C4···H14ⁱⁱⁱ	2.826 (10)
O1···C17	3.1263 (9)	C4···H12^vii	2.993 (10)
O1···C12ⁱ	3.2141 (10)	C5···H12^vii	2.817 (10)
O1···C15ⁱⁱ	3.2268 (8)	C7···H15	2.937 (9)
O2···N1	2.7902 (7)	C15···H16Aⁱⁱ	2.900 (9)
O2···C8	3.2091 (9)	C16···H16B^vi	2.987 (9)
O2···C1	3.3715 (8)	C16···H2	2.538 (9)
O2···C3^iv	3.3498 (10)	C17···H2	2.696 (9)
O2···C2	3.4103 (9)	H2···H16B	2.223 (12)
O1···H9	2.516 (9)	H5···H12^vii	2.444 (13)
O1···H16A	2.376 (9)	H5···H15ⁱⁱⁱ	2.509 (12)
O1···H4^v	2.806 (11)	H16B···H16B^vi	2.381 (13)

C6—S1—C7	98.19 (9)	C12—C11—Cl1	117.82 (16)
C17—O3—C18	116.60 (16)	C10—C11—Cl1	119.98 (16)
C8—N1—C1	124.52 (15)	C11—C12—C13	119.92 (19)
C8—N1—C16	115.56 (16)	C11—C12—H12	118.0 (16)
C1—N1—C16	118.47 (16)	C13—C12—H12	122.0 (16)
C2—C1—C6	118.60 (18)	C12—C13—C14	119.4 (2)
C2—C1—N1	121.41 (17)	C12—C13—H13	118.8 (16)
C6—C1—N1	120.00 (17)	C14—C13—H13	121.8 (16)
C3—C2—C1	120.63 (19)	C15—C14—C13	120.3 (2)
C3—C2—H2	120.0 (15)	C15—C14—H14	119.2 (16)
C1—C2—H2	119.4 (15)	C13—C14—H14	120.5 (16)
C4—C3—C2	120.6 (2)	C14—C15—C10	121.74 (18)
C4—C3—H3	120.2 (16)	C14—C15—H15	120.3 (15)
C2—C3—H3	119.2 (16)	C10—C15—H15	118.0 (15)
C3—C4—C5	119.4 (2)	N1—C16—C17	112.65 (16)
C3—C4—H4	120.0 (18)	N1—C16—H16A	109.1 (15)
C5—C4—H4	120.6 (18)	C17—C16—H16A	109.0 (14)
C4—C5—C6	120.5 (2)	N1—C16—H16B	109.1 (15)
C4—C5—H5	119.4 (15)	C17—C16—H16B	110.8 (15)
C6—C5—H5	120.1 (15)	H16A—C16—H16B	106 (2)
C5—C6—C1	120.27 (18)	O2—C17—O3	125.18 (19)
C5—C6—S1	119.21 (15)	O2—C17—C16	125.21 (18)
C1—C6—S1	120.51 (15)	O3—C17—C16	109.61 (16)
C9—C7—C8	118.34 (17)	O3—C18—C19	107.0 (2)
C9—C7—S1	125.50 (16)	O3—C18—H18A	106.6 (17)
C8—C7—S1	116.11 (14)	C19—C18—H18A	113.0 (17)
O1—C8—N1	120.36 (17)	O3—C18—H18B	109.1 (17)
O1—C8—C7	121.99 (17)	C19—C18—H18B	112.6 (18)
N1—C8—C7	117.64 (16)	H18A—C18—H18B	108 (2)
C7—C9—C10	127.75 (19)	C18—C19—H19A	111.0 (18)
C7—C9—H9	116.7 (15)	C18—C19—H19B	108 (2)
C10—C9—H9	115.3 (15)	H19A—C19—H19B	109 (3)
C15—C10—C11	116.42 (18)	C18—C19—H19C	112.1 (19)
C15—C10—C9	123.16 (17)	H19A—C19—H19C	107 (2)
C11—C10—C9	120.39 (18)	H19B—C19—H19C	111 (3)
C12—C11—C10	122.19 (19)

C8—N1—C1—C2	149.38 (19)	C9—C7—C8—N1	−152.68 (18)
C16—N1—C1—C2	−16.2 (3)	S1—C7—C8—N1	29.5 (2)
C8—N1—C1—C6	−31.3 (3)	C8—C7—C9—C10	175.30 (18)
C16—N1—C1—C6	163.13 (17)	S1—C7—C9—C10	−7.1 (3)
C6—C1—C2—C3	−0.8 (3)	C7—C9—C10—C15	37.4 (3)
N1—C1—C2—C3	178.55 (18)	C7—C9—C10—C11	−140.4 (2)
C1—C2—C3—C4	0.8 (3)	C15—C10—C11—C12	−2.9 (3)
C2—C3—C4—C5	0.3 (3)	C9—C10—C11—C12	175.1 (2)
C3—C4—C5—C6	−1.3 (3)	C15—C10—C11—Cl1	178.57 (15)
C4—C5—C6—C1	1.2 (3)	C9—C10—C11—Cl1	−3.5 (3)
C4—C5—C6—S1	−178.03 (16)	C10—C11—C12—C13	1.7 (3)
C2—C1—C6—C5	−0.2 (3)	Cl1—C11—C12—C13	−179.76 (18)
N1—C1—C6—C5	−179.53 (17)	C11—C12—C13—C14	0.7 (3)
C2—C1—C6—S1	179.07 (15)	C12—C13—C14—C15	−1.8 (3)
N1—C1—C6—S1	−0.3 (2)	C13—C14—C15—C10	0.5 (3)
C7—S1—C6—C5	−146.23 (16)	C11—C10—C15—C14	1.8 (3)
C7—S1—C6—C1	34.53 (17)	C9—C10—C15—C14	−176.10 (19)
C6—S1—C7—C9	134.12 (18)	C8—N1—C16—C17	−80.3 (2)
C6—S1—C7—C8	−48.28 (16)	C1—N1—C16—C17	86.5 (2)
C1—N1—C8—O1	−165.71 (18)	C18—O3—C17—O2	−0.1 (3)
C16—N1—C8—O1	0.3 (3)	C18—O3—C17—C16	−179.95 (18)
C1—N1—C8—C7	14.8 (3)	N1—C16—C17—O2	1.2 (3)
C16—N1—C8—C7	−179.20 (16)	N1—C16—C17—O3	−179.02 (16)
C9—C7—C8—O1	27.9 (3)	C17—O3—C18—C19	−171.0 (2)
S1—C7—C8—O1	−149.91 (15)